LU82072A1 - GRANULATION PROCESS FOR TRANS-D1-1-HYDROXY-3- (1 ', 1'-DIMETHYLHEPTYL) -6,6-DIMETHYL-6A, 7,8,9,10,10A-HEXAHYDROBENZO (B, D) PYRAN -9-ONE (NABILONE) - Google Patents
GRANULATION PROCESS FOR TRANS-D1-1-HYDROXY-3- (1 ', 1'-DIMETHYLHEPTYL) -6,6-DIMETHYL-6A, 7,8,9,10,10A-HEXAHYDROBENZO (B, D) PYRAN -9-ONE (NABILONE) Download PDFInfo
- Publication number
- LU82072A1 LU82072A1 LU82072A LU82072A LU82072A1 LU 82072 A1 LU82072 A1 LU 82072A1 LU 82072 A LU82072 A LU 82072A LU 82072 A LU82072 A LU 82072A LU 82072 A1 LU82072 A1 LU 82072A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- nabilone
- ethanol
- trans
- hydroxy
- dimethyl
- Prior art date
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- GECBBEABIDMGGL-RTBURBONSA-N nabilone Chemical compound C1C(=O)CC[C@H]2C(C)(C)OC3=CC(C(C)(C)CCCCCC)=CC(O)=C3[C@@H]21 GECBBEABIDMGGL-RTBURBONSA-N 0.000 title claims description 18
- 229960002967 nabilone Drugs 0.000 title claims description 18
- 238000005469 granulation Methods 0.000 title claims description 10
- 230000003179 granulation Effects 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 5
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 title description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 11
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims 1
- 239000006185 dispersion Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229920002472 Starch Polymers 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000000049 anti-anxiety effect Effects 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Otolaryngology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
Description
_ --Ï »_ --Ï "
La nabilone [trans-dl-l-hydroxy-3-(1',1’-diméthyl-heptyl)-6,6-diméthyl-6a,7,8,9,10,10a-hexahydrobenzo[b,d[pyran- 9-one] fait partie d'un groupe d'intermédiaires utiles =· préparés par Farenholtz, et al·, J. Am. Chem. Soc., 88, 2079 5 (1966) , 8_9, 5934 (1967) pour la préparation du Δ^-THC (tetra- • hydrocannibinol) et de ses homologues alkylés comportant des groupements alkyle de 1 à 10 atomes de carbone sur le carbone 9 C-3. (Δ -THC est le trans-dl-l-hydroxy-3-n-pentyl-6,6,9-trimëthyl-6a,7,8,10a-têtrahydrobenzo[b,d]pyrrane). Dans les 10 brevets des E.U.A. N° 3.928.598, 3.953.603, 3.946.673 et * 3.998.188, Archer indique que la nabilone, en plus d'être un "intermédiaire utile", a une activité comme médicament antidépresseur, anti-anxiété, analgésique et/ou sédatif, et Archer et Lemberger ont en outre étendu ces actions utiles à 15 celle d'anti-émétique et à l'action pour le traitement des glaucomes, voir les brevets des E.U.A. N° 4.087.545 et 4.087.547. La nabilone n'est pas bien absorbée par l'intestin pendant l'administration orale. Thakker et al., J. Pharm. Pharroac., 29, 783 (1977) décrivent certaines compositions 20 utiles de la nabilone, comprenant une dispersion dans la polyvinylpyrrolidinone. Thakker et al. mélangent la nabilone avec la PVP dans un rapport de 1:2-20 dans un solvant comme l'éthanol puis chassent le solvant par évaporation sous vide. Le produit ainsi obtenu est un solide vitreux qui doit 25 d'abord être brisé puis réduit en une poudre fine pour le disperser uniformément dans d'autres excipients pharmaceutiques avant son introduction dans des capsules de gélatine s'emboîtant.Nabilone [trans-dl-1-hydroxy-3- (1 ', 1'-dimethyl-heptyl) -6,6-dimethyl-6a, 7,8,9,10,10a-hexahydrobenzo [b, d [pyran - 9-one] is part of a group of useful intermediaries = · prepared by Farenholtz, et al ·, J. Am. Chem. Soc., 88, 2079 5 (1966), 8_9, 5934 (1967) for the preparation of Δ ^ -THC (tetra- • hydrocannibinol) and its alkylated counterparts having alkyl groups of 1 to 10 carbon atoms on the carbon 9 C-3. (Δ -THC is trans-dl-1-hydroxy-3-n-pentyl-6,6,9-trimethyl-6a, 7,8,10a-tetrahydrobenzo [b, d] pyrran). In the 10 U.S. patents N ° 3.928.598, 3.953.603, 3.946.673 and * 3.998.188, Archer indicates that nabilone, in addition to being a "useful intermediary", has an activity like antidepressant drug, anti-anxiety, analgesic and / or sedative, and Archer and Lemberger have further extended these useful actions to that of antiemetic and to the action for the treatment of glaucoma, see US Patents N ° 4.087.545 and 4.087.547. Nabilone is not well absorbed from the intestine during oral administration. Thakker et al., J. Pharm. Pharroac., 29, 783 (1977) describe certain useful compositions of nabilone, comprising a dispersion in polyvinylpyrrolidinone. Thakker et al. mix the nabilone with the PVP in a ratio of 1: 2-20 in a solvent such as ethanol and then remove the solvent by evaporation under vacuum. The product thus obtained is a glassy solid which must first be broken up and then reduced to a fine powder in order to disperse it uniformly in other pharmaceutical excipients before its introduction into interlocking gelatin capsules.
Cette invention est un procédé permettant de 30 fournir une composition de granulation pour la nabilone qui évite les défauts et les difficultés de la dispersion solide * susmentionnée de Thakker et al.This invention is a method of providing a granulation composition for nabilone which avoids the defects and difficulties of the aforementioned solid dispersion * of Thakker et al.
En particulier, l'invention fournit une solution de nabilone et de polyvinylpyrrolidone dans l'éthanol, en tant 35 que solution de granulation. Cette solution est ensuite utilisée pour granuler des excipients et supports pharmaceutiques comme l'amidon, le lactose, la cellulose, etc. Après séchage et broyage, le matériau granulé en poudre i 2 peut être mélange avec d'autres matériaux pour préparer une composition que l'on peut introduire dans des capsules de gélatine s'emboîtant comme prévu. En d'autres termes, la dispersion nabilone-PVP de Thakker et al est formée in situ * 5 comme composant de granulation pour des excipients qui sont insolubles dans l'éthanol. Le rapport de la nabilone à la PVP, * dans la nouvelle composition de granulation comme dans les dispersions de Thakker et al, est de une partie de nabilone pour deux à vingt parties de PVP.In particular, the invention provides a solution of nabilone and polyvinylpyrrolidone in ethanol, as a granulation solution. This solution is then used to granulate excipients and pharmaceutical carriers such as starch, lactose, cellulose, etc. After drying and grinding, the granulated powder material i 2 can be mixed with other materials to prepare a composition which can be introduced into gelatin capsules which fit together as intended. In other words, the nabilone-PVP dispersion of Thakker et al is formed in situ * 5 as a granulation component for excipients which are insoluble in ethanol. The ratio of nabilone to PVP, * in the new granulation composition as in the dispersions of Thakker et al, is one part of nabilone for two to twenty parts of PVP.
10 Un produit de granulation ainsi préparé a une excellente stabilité en ce qui concerne la nabilone, et les * données de dissolution montrent que la granulation est équivalente à la dispersion de Thakker et al préparée sous forme d'un verre dans 1'évaporateur rotatif puis pulvérisée.A granulation product thus prepared has excellent stability with respect to nabilone, and the dissolution data show that the granulation is equivalent to the dispersion of Thakker et al prepared as a glass in the rotary evaporator and then sprayed.
15 On a montré chez les chiens une disponibilité biologique équivalente pour la composition granulée de cette invention par rapport à la dispersion de Thakker et al.Equivalent biological availability for the granulated composition of this invention has been shown in dogs compared to the dispersion of Thakker et al.
D'autres dispersions de nabilone préparées par Thakker et al, comprenant une dans le polyéthylèneglycol, 2 0 peuvent être préparées de même in situ sur l'exc.'. ient particulier en utilisant le nouveau procédé tel que décrit pour la dispersion de nabilone et de PVP ci-dessus : solution dans l'éthanol puis granulation d'un excipient insoluble dans 1'éthanol.Other dispersions of nabilone prepared by Thakker et al, including one in polyethylene glycol, can also be prepared in situ on exc. '. ient particular using the new process as described for the dispersion of nabilone and PVP above: solution in ethanol then granulation of an excipient insoluble in ethanol.
* 25 Cette invention est en outre illustrée par l'exemple spécifique suivant.* 25 This invention is further illustrated by the following specific example.
EXEMPLE 1EXAMPLE 1
On dissout cinq grammes de nabilone dans 125 ml d’éthanol anhydre et on y dissout 45 g de polyvinylpyrrolidone 30 (PVP). On ajoute la solution visqueuse résultante à 450 g de poudre fluide d'amidon dans un malaxeur Hobart. On utilise une petite quantité d'éthanol anhydre supplémentaire pour " introduire par rinçage le reste de la solution nabilone- PVP dans le malaxeur. Après un malaxage soigneux, on tamise 35 à l'état humide le produit granulé sur un tamis d’une ouverture de maille de 4,76 mm (on peut également utiliser un tamis d'une ouverture de maille de 3,36 mm).Le produit granulé tamisé est séché à l'air puis broyé jusqu'à la h r , 3 granulométrie désirée dans un broyeur à boulets.Five grams of nabilone are dissolved in 125 ml of anhydrous ethanol and 45 g of polyvinylpyrrolidone 30 (PVP) are dissolved therein. The resulting viscous solution is added to 450 g of fluid starch powder in a Hobart mixer. A small amount of additional anhydrous ethanol is used to "rinse" the remainder of the nabilone-PVP solution into the kneader. After careful kneading, the granulated product is sieved wet through an open sieve of 4.76 mm mesh (a sieve with a 3.36 mm mesh opening can also be used). The sieved granulated product is air dried and then ground to the hr, 3 desired particle size in a ball mill.
Une granulation nabilone-PVP-amidon ainsi préparée peut être ensuite mélangée a d'autres excipients pour obtenir un mélange final ayant la concentration désirée en nabilone * 5 en vue de son introduction dans des capsules de gélatine s'emboîtant vides.A nabilone-PVP-starch granulation thus prepared can then be mixed with other excipients to obtain a final mixture having the desired concentration of nabilone * 5 with a view to its introduction into empty interlocking gelatin capsules.
‘ On peut utiliser d'autres excipients insolubles dans l'éthanol, comme le lactose, le mannitol et le dextrose, à la place de l'amidon fluide pour préparer le produit granulé 10 précédent.‘Other excipients insoluble in ethanol, such as lactose, mannitol and dextrose, can be used in place of the fluid starch to prepare the preceding granulated product.
♦ ♦ 1 «♦ ♦ 1 "
Claims (2)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1981079 | 1979-03-09 | ||
| US06/019,810 US4195078A (en) | 1979-03-09 | 1979-03-09 | Nabilone granulation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU82072A1 true LU82072A1 (en) | 1980-04-23 |
Family
ID=21795156
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU82072A LU82072A1 (en) | 1979-03-09 | 1980-01-10 | GRANULATION PROCESS FOR TRANS-D1-1-HYDROXY-3- (1 ', 1'-DIMETHYLHEPTYL) -6,6-DIMETHYL-6A, 7,8,9,10,10A-HEXAHYDROBENZO (B, D) PYRAN -9-ONE (NABILONE) |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4195078A (en) |
| EP (1) | EP0015635A1 (en) |
| JP (1) | JPS55133309A (en) |
| AU (1) | AU531805B2 (en) |
| BE (1) | BE881049A (en) |
| CA (1) | CA1124178A (en) |
| CH (1) | CH643840A5 (en) |
| DK (1) | DK8080A (en) |
| FR (1) | FR2450606A1 (en) |
| GB (1) | GB2045080B (en) |
| IE (1) | IE49243B1 (en) |
| IL (1) | IL59098A (en) |
| IT (1) | IT1193886B (en) |
| LU (1) | LU82072A1 (en) |
| NZ (1) | NZ192557A (en) |
| ZA (1) | ZA80104B (en) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4327080A (en) * | 1981-07-13 | 1982-04-27 | E. R. Squibb & Sons, Inc. | Novel Bendroflumethiazide formulations and method |
| JPS59155309A (en) * | 1983-02-22 | 1984-09-04 | Teijin Ltd | Active type vitamin d3 composition and its preparation |
| NZ211545A (en) * | 1984-04-11 | 1987-09-30 | Ici Australia Ltd | Composition having particulate trace element suspended in matrix of solid polyethylene glycol |
| US4818539A (en) * | 1985-02-05 | 1989-04-04 | Warner-Lambert Company | Ingestible aggregate and delivery system prepared therefrom |
| US4851392A (en) * | 1985-02-05 | 1989-07-25 | Warner-Lambert Company | Ingestible aggregate and delivery system prepared therefrom |
| US4790991A (en) * | 1985-02-05 | 1988-12-13 | Warner-Lambert Company | Ingestible aggregate and delivery system prepared therefrom |
| US4843098A (en) * | 1985-02-05 | 1989-06-27 | Warner-Lambert Company | Ingestible aggregate and delivery system prepared therefrom |
| US4747881A (en) * | 1985-02-05 | 1988-05-31 | Warner-Lambert Company | Ingestible aggregate and delivery system prepared therefrom |
| US4844908A (en) * | 1986-11-27 | 1989-07-04 | Duphar International Research B.V. | Method of preparing tablets with clovoxamine fumarate and tablets thus prepared |
| EP0547796A1 (en) * | 1991-12-17 | 1993-06-23 | Konica Corporation | Solid chemicals for processing silver halide photographic light-sensitive material |
| US6566560B2 (en) | 1999-03-22 | 2003-05-20 | Immugen Pharmaceuticals, Inc. | Resorcinolic compounds |
| US6541510B2 (en) * | 2000-09-28 | 2003-04-01 | Immugen Pharmaceuticals, Inc. | Antiviral methods and compounds |
| US20020137802A1 (en) * | 2000-09-28 | 2002-09-26 | Travis Craig R. | Methods and compounds for inhibiting eicosanoid metabolism and platelet aggregation |
| WO2003080043A1 (en) * | 2002-03-18 | 2003-10-02 | Immugen Pharmaceuticals, Inc. | Topical formulations of resorcinols and cannibinoids and methods of use |
| CA2845443A1 (en) * | 2014-03-04 | 2015-09-04 | Pharmascience Inc. | Orally disintegrating tablet of nabilone and method of manufacturing |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR886435A (en) * | 1941-09-29 | 1943-10-14 | Advanced knitting needle | |
| US3136692A (en) * | 1961-06-30 | 1964-06-09 | Strong Cobb Arner Inc | Effervescent composition containing polyvinylpyrrolidone |
| DE1467792A1 (en) * | 1965-05-21 | 1968-12-12 | Brunnengraeber & Co Gmbh Dr Ch | Disintegrants for pharmaceutical pellets |
| CA885974A (en) * | 1968-04-02 | 1971-11-16 | Mowatt And Moore Limited | Ferrous fumarate capsule and preparation |
| IL32673A (en) * | 1968-08-05 | 1973-11-28 | Ciba Geigy Ag | A granular material containing oily or liquid therapeutically usable furanosides and a process for its manufacture |
| US3632778A (en) * | 1970-06-10 | 1972-01-04 | Hoffmann La Roche | Tablets containing l-dopa |
| NL7112288A (en) * | 1970-09-16 | 1972-03-20 | ||
| JPS5418330B2 (en) * | 1973-03-16 | 1979-07-06 | ||
| US3851032A (en) * | 1973-04-23 | 1974-11-26 | Sterling Drug Inc | Process of preparing a solid fine crystalline paracetamol polymer complex composition |
| US3864492A (en) * | 1973-08-01 | 1975-02-04 | Abbott Lab | Method of treating depression using 1,4{40 -dihydroxy-3-n-pentyl-6,6,9-trimethyl-6a,7,10,10a-tetra-hydrodibenzo{8 b,d{9 pyran |
| IE39678B1 (en) * | 1973-11-05 | 1978-12-06 | Lilly Co Eli | A polymorphic form of a dibenzopyranone |
| US3944673A (en) * | 1973-11-05 | 1976-03-16 | Eli Lilly And Company | Hexahydro-dibenzo[b,d]pyran-9-ones as analgesic drugs |
| US3987188A (en) * | 1973-11-05 | 1976-10-19 | Eli Lilly And Company | Hexahydro-dibenzo[b,d]pyran-9-ones as sedative drugs |
| US3920809A (en) * | 1973-11-05 | 1975-11-18 | Lilly Co Eli | Dibenzo(b,d)pyranone dispersions |
| US4024275A (en) * | 1973-11-05 | 1977-05-17 | Eli Lilly And Company | Method of reducing elevated blood pressure with dihydroxy-hexahydrodibenzo(b,d)pyrans |
| US3953603A (en) * | 1973-11-05 | 1976-04-27 | Eli Lilly And Company | Hexahydro-dibenzo[b,d,]pyran-9-ones as psychotropic, particularly anti-depressant drugs |
| AT329556B (en) * | 1974-10-24 | 1976-05-25 | Lilly Co Eli | PROCESS FOR PRODUCING A NEW STABLE POLYMORPHIC CRYSTALLINE FORM OF 1-HYDROXY-3- (1 ', 1'-DIMETHYLHEPTYL) -6,6-DIMETHYL-6,6A, 7,8,10,10A-HEXAHYDRO-9H-DIBENZO ( B, D) PYRAN-9-ON |
| US4143129A (en) * | 1975-10-11 | 1979-03-06 | Lilly Industries Limited | Cephalexin tablets |
| US4088777A (en) * | 1976-02-17 | 1978-05-09 | Eli Lilly And Company | Hexahydro-dibenzo[b,d]pyran-9-ones as anticonvulsant drugs |
| US4087546A (en) * | 1976-02-17 | 1978-05-02 | Eli Lilly And Company | Hexahydro-dibenzo[b,d]pyran-9-ones as antiasthmatic drugs |
| US4087545A (en) * | 1976-02-17 | 1978-05-02 | Eli Lilly And Company | Hexahydro-dibenzo[b,d]pyran-9-ones as antiemetic drugs |
| US4087547A (en) * | 1976-02-17 | 1978-05-02 | Eli Lilly And Company | Hexahydro-dibenzo[b,d]pyran-9-ones in treatment of glaucoma |
-
1979
- 1979-03-09 US US06/019,810 patent/US4195078A/en not_active Expired - Lifetime
-
1980
- 1980-01-08 NZ NZ192557A patent/NZ192557A/en unknown
- 1980-01-08 DK DK8080A patent/DK8080A/en not_active Application Discontinuation
- 1980-01-08 ZA ZA00800104A patent/ZA80104B/en unknown
- 1980-01-08 CA CA343,252A patent/CA1124178A/en not_active Expired
- 1980-01-09 IT IT19114/80A patent/IT1193886B/en active
- 1980-01-09 CH CH13880A patent/CH643840A5/en not_active IP Right Cessation
- 1980-01-09 BE BE1/9675A patent/BE881049A/en not_active IP Right Cessation
- 1980-01-09 FR FR8000430A patent/FR2450606A1/en active Granted
- 1980-01-09 IL IL59098A patent/IL59098A/en not_active IP Right Cessation
- 1980-01-10 EP EP80300094A patent/EP0015635A1/en not_active Ceased
- 1980-01-10 JP JP172880A patent/JPS55133309A/en active Granted
- 1980-01-10 IE IE42/80A patent/IE49243B1/en not_active IP Right Cessation
- 1980-01-10 LU LU82072A patent/LU82072A1/en unknown
- 1980-01-10 GB GB8000871A patent/GB2045080B/en not_active Expired
- 1980-01-11 AU AU54554/80A patent/AU531805B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| GB2045080A (en) | 1980-10-29 |
| BE881049A (en) | 1980-07-09 |
| CH643840A5 (en) | 1984-06-29 |
| ZA80104B (en) | 1981-08-26 |
| JPH0142923B2 (en) | 1989-09-18 |
| AU5455480A (en) | 1980-09-11 |
| AU531805B2 (en) | 1983-09-08 |
| IT1193886B (en) | 1988-08-31 |
| IT8019114A0 (en) | 1980-01-09 |
| DK8080A (en) | 1980-09-10 |
| FR2450606B1 (en) | 1983-04-15 |
| EP0015635A1 (en) | 1980-09-17 |
| IL59098A0 (en) | 1980-05-30 |
| GB2045080B (en) | 1983-05-25 |
| IE49243B1 (en) | 1985-09-04 |
| JPS55133309A (en) | 1980-10-17 |
| IE800042L (en) | 1980-09-09 |
| IL59098A (en) | 1983-09-30 |
| FR2450606A1 (en) | 1980-10-03 |
| NZ192557A (en) | 1981-05-01 |
| CA1124178A (en) | 1982-05-25 |
| US4195078A (en) | 1980-03-25 |
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